You might try this one, they are reputable. Have a look at this tour, it is for this year but I imagine there are others planned. http://www.amadirectlink.com/travel/Route66.asp
If you look at the Home page there are big names associated with the group.
Hope this helps. Prices seem reasonable and less than you mentioned, but this is with your own bike of course.

For rental they recommend this company. It is based in Chicago.
http://www.eaglerider.com/
They also do guided tours of Route 66.

hi

I have just done a bit of Route 66 on a Harley - from Kingman Arizona to Williams, which is a lovely bit of road

we used eagle rider too

its pretty easy to do your own thing, we just booked hotels as we turned up or booked ahead on the day.

Blimey, there must gonna be hundreds of blokes in their 50's heading to Route 66.

My mates and myself have been planning it for about 2 years now!! (we're very slow)

This is because we all turn 50 in two years time. We've been looking at the Harley Davidson Club through the Harley website and you're right....its about £4k. This includes all accommadation and a guide and the total route from Chicago to LA.

This is my mates Harley........I'm well jealous!!

Sorry spinner cannot see your photo It seems we may all meet up
I suppose its not a bad price really, but a bit of a shock, hotels and hiring bikes etc wont be cheap, and it is a holiday of a life time. Who are you booking it with, which company?

I live about a mile from part of Route 66 in the LA area. I often see people on Harley's riding down there. In fact, it's often several Harley's at once! There are lots of nostalgic places along Route 66 too. This is just close to where I live, but there are at least three 1950's style diners (deliberately made to look old) and there is also a drive-in movie theater (that, I must confess, I have yet to go to). And that's just the stuff that's close to me... I'm sure many parts of Route 66 in all of the states in goes through have these nostalgic locations. You should definitely do it... it's a great way to see multiple states in one trip.

if youre an experienced biker, then id really look into doing it yourself

it would be a nightmare to be stuck on someone elses schedule

theres days when you just get tired and need a 2 night stop

Eagle rider worked out at £450 for 5 days inc all the insurances and petrol etc

Motels are about $50-$150 ish a night